Sean Penn plays Harvey Milk as a man who knows exactly what he is getting into. He does not pretend the fight for gay rights is clean or safe. He plays Milk as a salesman, a street fighter and a father figure, all at once. That performance carries Milk, Gus Van Sant’s 2008 biopic about the first openly gay man elected to public office in California.
Penn’s Milk is funny, blunt and terrified. He knows the clock is running. He records his will nine days before the assassinations of November 27, 1978, and the film keeps returning to that tape, flashing back to his arrival in San Francisco in 1972 and his rise from Castro Camera store owner to city supervisor. It is a story about losing friends, winning seats and losing them again, told in fragments that keep circling back to the moment of death.
Trailer, via Focus Features.
The Long Road to the Screen
The road to Milk was long. A 1984 documentary, The Times of Harvey Milk, based on Randy Shilts’s 1982 biography The Mayor of Castro Street, had already covered the story. That film won the Academy Award for Best Documentary Feature for 1984 and took Special Jury Prize at the first Sundance Film Festival. Scripts came and went in the early 1990s. None stuck until 2007, when Van Sant attached himself to the project and Dustin Lance Black wrote the script.
Much of the film was shot on Castro Street and other San Francisco locations, including Milk’s former storefront, Castro Camera. The production aimed for authenticity, and the city itself becomes a character in the story.
Penn and Brolin Carry the Weight
Penn’s performance is the center of the film. He plays Milk as a man who has made a bargain with the world: he will fight for gay rights, and he will do it openly, even though the cost is certain. The scene where he records his will is a masterclass in restraint. Penn does not cry. He speaks plainly, lists names and leaves instructions, and the weight of the moment lands on the audience rather than on the actor.
Josh Brolin plays Dan White, the former police officer and firefighter who assassinates Milk and Mayor George Moscone. Brolin’s White is not a cartoon villain. He is a man who believes he is doing God’s work, and the film spends enough time with him to make that belief feel real. The contrast between the two men — Milk’s warmth and White’s coldness — is the engine of the story.
The Cast Around Them
Emile Hirsch plays Cleve Jones, Milk’s chief lieutenant and the designer of the pink triangle banner. Diego Luna plays Jack Lira, a sweet-natured but unbalanced young man who cannot handle Milk’s devotion to politics and eventually hangs himself. James Franco plays Scott Smith, Milk’s first love, who serves as his campaign manager but grows frustrated with Milk’s focus on activism and leaves him. Alison Pill plays Anne Kronenberg, Milk’s trusted aide, and Victor Garber plays Mayor Moscone.
The film also brings in real-life figures who worked with Milk. Frank M. Robinson, Allan Baird and Tom Ammiano appear as themselves. Carol Ruth Silver, who served with Milk on the Board of Supervisors and was allegedly also a target of the assassination, plays a small role as Thelma. Cleve Jones has a small role as Don Amador. Anne Kronenberg appears as a stenographer, and Daniel Nicoletta appears as Carl Carlson.
The Politics of the Time
The film is careful about its history. It shows Milk’s three unsuccessful attempts to become a city supervisor for the California State Assembly before he finally wins a seat on the San Francisco Board of Supervisors in 1977, after a change from at-large elections to district elections. His victory makes him the first openly gay man to be voted into major public office in California and the third openly homosexual politician in the entire United States.
The film also captures the resistance Milk faced in the Castro, a working-class neighborhood that was once Irish-Catholic and was evolving into a predominantly gay neighborhood. Milk uses his business background to become a gay activist, eventually becoming a mentor to Cleve Jones. The clash with the local gay establishment, which he feels is too cautious, is a central thread of the story.
Where It Falls Short
Milk is not a perfect film. Some scenes feel padded, and the flashbacks can lose momentum. The film’s structure is deliberate, but it sometimes sacrifices pace for emotional weight. The middle stretch, where Milk builds his coalition and loses Smith, could have been tighter.
The film also leans on a familiar structure of triumph and tragedy. It is a story about a man who wins and then loses, and the ending is inevitable from the first frame. That does not mean it fails. It means the film is honest about its subject.
The Final Word
Milk is a powerful portrait of a man who refused to hide. Penn’s performance is the highlight, and Brolin’s White gives him a worthy opponent. The supporting cast is strong, and the film’s attention to historical detail adds weight to the personal story.
The film’s tagline, “Never blend in,” sums up its attitude. Milk did not want to fit in. He wanted to change the room. The film honors that ambition without softening it.
“Never blend in.”
8.3 out of 10.
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